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Modafinil synthesis process

a technology of modafinil and synthesis process, which is applied in the field of synthesis process of modafinil, can solve the problems of difficult control, sulphone by-product (ii) which is difficult to separate from modafinil, and the preparation process, however, has drawbacks

Inactive Publication Date: 2009-06-02
TEVA SANTE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

"The present invention provides a process for obtaining modafinil in the form of particles with defined granulometry, and in a single polymorph. This process allows for the selective obtainment of different polymorphs of modafinil without the need for a purification step. The resulting modafinil is pure (>99.5%) and has high yields."

Problems solved by technology

The drawback of this process is that the step of oxidizing the sulphur of the 2-[(diphenylmethyl)thio]acetamide intermediate in the presence of hydrogen peroxide is difficult to control and may lead to the formation of a sulphone by-product (II) which is difficult to separate from the modafinil.
This preparation process, however, has drawbacks.
In particular it involves a plurality of steps of recrystallization of the modafinil obtained, and presents a mediocre yield.

Method used

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  • Modafinil synthesis process

Examples

Experimental program
Comparison scheme
Effect test

example 1

1-Liter Scale Procedure

[0107]A 1-liter reactor of type SIMULAR (Hazard Evaluation Laboratory, HEL) equipped with an impeller stirrer and a gas introduction tube was charged with 150 g of DMSAM, 450 ml of methanol and 33 mL of water. The suspension was stirred at 100 rpm and 20° C. for 10 min and then heated to 35° C. to dissolve the solids. The solution was subsequently stirred at 200 rpm for 10 min, then cooled to 25° C. and stirred at 350 rpm and at this temperature for 20 min.

[0108]46.8 g of ammonia were then introduced over 4.5 h at 25° C.

[0109]The reaction medium was left in contact for 10 h at 25° C. with stirring at 350 rpm before finally being cooled to −10° C. and then filtered over a frit of porosity 3.

[0110]The moist product was then dried under vacuum at 45° C.

[0111]Yield=89%, median=34.1 μm.

examples 2 to 5

Effect of temperature and Stirring Speed on Granulometry

example 2

Standard (Zero-Point) Experiment and Reproducibility

[0112]Conditions of standard experiment were the same as those of example 1.

[0113]The point at which the ammonia was injected, the jacket temperature, the cooling rate and the contact time at −10° C. were maintained constant during the various experiments, since these parameters had little or no influence on controlling the granulometry of the modafinil synthesized.

[0114]A standard experiment was desired in order to obtain a final granulometric median which was situated in the range 15-45 μm and thus to constitute a zero point of comparison for the subsequent experiments.

[0115]This search then culminates in the following conditions:[0116]reaction temperature T=25° C.,[0117]stirring speed SS=350 rpm,[0118]ammonia introduction time t=4.5 h.

[0119]Under these conditions the granulometric median obtained, G, was 34 μm.

[0120]This standard experiment was then repeated in order to assess its reproducibility: that was, three experiments con...

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Abstract

The invention relates to a process for preparing modafinil having a defined granulometry which comprises the steps of: a) preparing a solution of DMSAM; b) contacting the solution obtained with NH3 at a predetermined temperature and a predetermined stirring; and c) isolating the modafinil formed, wherein said temperature and said stirring are predetermined in order to obtain said defined granulometry.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]This application represent entry into the U.S. national phase of International Application No. PCT / IB2004 / 001409, filed May 5, 2004, which in turn claims priority of European Application No. EP 03 291 152.1, filed May 16, 2003.FIELD OF THE INVENTION[0002]The present invention is directed to a process for preparing modafinil having a defined granulometry.BACKGROUND OF THE INVENTION[0003]Modafinil (C15H15NO2S) of formula I, 2-(benzhydrylsulphinyl)-acetamide, is a synthetic acetamide derivative possessing wakefulness-promoting activity, whose structure has been described in U.S. Pat. No. 4,177,290 and whose racemic form has received the approval of the registration authorities for use in the treatment of narcolepsy.[0004][0005]Example 1 (scheme 1) of U.S. Pat. No. 4,177,290 (Lafon) describes a process for preparing modafinil which comprises reacting benzhydrylthioacetic acid with thionyl chloride in a first step. The acid chloride obtained i...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): C07C231/24C07C231/02C07C315/04C07C315/06
CPCC07C315/04C07C317/44C07B2200/13C07C315/06C07C317/28C07C317/50A61K31/165
Inventor ROSE, SEBASTIEN
Owner TEVA SANTE
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